Your Guide to Sailing the Cyclades

We’re not usually fond of hyperbole but the Cyclades islands have so much to boast about.

Here is the  the cradle of Western civilisation, from Athens to Troy to Milos. In this Aegean Sea there are over 1000 islands and just as many places to drop anchor. Long shorelines. Uninhabited islets. Traditional villages. Ancient ruins. Beaches without footprints.

If you like yachts you’ll love the Aegean Sea. If you like exploring you’ll love the Cyclades islands, even if you don’t know port from starboard. Here’s a brief guide to the possibility.

First, A Warning About Sailing the Aegean Sea

Sailing past the island of Kynthos. Ready to explore?

Beware. The notorious Meltemi wind dominates the Aegean Sea. Blowing from north to northwest it provides perfect sailing conditions for most of the year. However, it’s often gale force between July and September. Did you ever wonder why Mykonos has so many windmills?

Unfortunately, people don’t appreciate this wind. They want to sail the Cyclades and end up stuck in a Mykonos port for seven days because the wind won’t relent. This region is incredible…but if you want to sail during these midsummer months head to the Dalmatian Coast between Croatia and Montenegro, or explore Greece’s Ionian islands instead.

Imagine Chartering a Yacht Between These Destinations

Athens Athens is well connected and well, it’s Athens. So before setting sail you can explore ancient history and then so much more.

Need Advise on Yacht Charters?

Cape Sounion – Hundreds of coach tours block the road to the iconic Temple of Poseidon. Avoid them and explore this cape properly, by yacht.

Poros is perfect for a couple of quiet sailing days. Who will you travel with?

Poros – Poseidon ruled over the kingdom of the sea. So it’s good to have him on your side. Poros was his home, where the main port is beautifully Venetian and you can drop anchor near so many picturesque beaches and villages.

Hydra – After tranquil Poros dock in Hydra, a fashionable and popular island where the only means of transportation are yachts and donkeys.

Explore the west side of Spetses island. Imagine dropping anchor here.

Spetses – Now for some lovely secluded bays and sandy beaches. Perhaps with some traditional villages and stone-paved alleyways. Spetses is the kind of island you really can’t explore without your own yacht.

Kea – The green island, dominated by oak trees, almond forests, valleys and ravines. Go for the change of scenery and don’t miss ancient cities like Karthea.

Kynthos – This island of Apollo is an underrated gem, where white houses shimmer above a turquoise sea and pink bougainvilleas weave up the mountainsides. It has some of the finest sunset anchorage positions in the Mediterranean.

Mykonos – Mykonos is a big island and the areas developed during the 1970s tourism boom are best avoided. The best beaches and wind are on the southern side, but also consider Avios Sostis if you want a quieter option.

Naoussa town, Paros island. This can be where you stop for the night.

Paros – At the heart of the Cyclades, this island symbolises why the Aegean is such a fine sailing destination. Whitewashed villages. Deserted sandy beaches. Clear waters and bays. Privacy and exclusivity, but also a sense of tradition.

SantoriniSantorini isn’t more beautiful than Milos. It’s just on Instagram a lot more. While it’s the place to be seen, the harbours are far below the villages, so it’s not the best island when you’re cruising. Of course, with a yacht charter you can explore Santorini’s less accessible places.

Ready to sail around Milos?

Milos – Now that Santorini is overcrowded, explorers are finally discovering Milos, an island of surprises and volcanic charms. Its coastline can captivate you for many days. It’s really a low-key alternative to its more famous sister island.

Ready to Sail?

We could list a dozen different yachts for charter. But most yachts are unique and the one you want might be somewhere else for when you want to travel.

So first think about where you might want to go. And when. Then our travel designers can talk you through the different yachts, prices, route options and more.

And remember our warning. The Cyclades are best avoided between July and September, even if many other agents won’t tell you this. But in April, May and October there’s nowhere better in the world to sail than here. June is pretty good as well.

Warm, sunny days. Crystal clear waters. Over a thousand islands. This can be your playground.

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